Here's lookin' at you kid
by lylame
Summary: Tristan has to make amends and it sparks an unexpected friendship.
1. Chapter 1: The beginning

**Disclaimer: ** I do not own the characters created by Amy Sherman Palladino

**Scenario: ** What if Tristan was forced to write a letter to Rory. What would she do?

Dear Rory,

If I were still allowed to gamble, I would wager you thought you had heard the last from me. I most impose on your time one last time. It is well known that as part the terms of the court, in lou of probation or jail time I was sent to military school. What is less known is that I have to attend so many hours of therapy. Some old woman in black robes has decided that I need to get in touch with my emotions to figure out why ' a young man with the world at his feet and all the opportunities money and social class can provide would throw it away for a thrill of adrenaline rush.'

My therapist comes with the best credentials money can buy. However, I doubt my parents have ever met the man. He is short, fat, with a comb over and aversion to deodorant. I provided the description because I hope you would find it amusing and because he is reading this letter.

He has suggested I work on righting the wrongs, like I am in a twelve-step program and he is my AA sponsor. Since I can't make it to Hartford and talk to you in person this is the only means at my disposal to reach you. Of all of our classmates, you were the only person I could bring myself to write to.

I know, that although I have never earned it, you would keep my confidence. You were always like that; everybody could tell from the first moment they saw you at Chilton that you were such an innocent nice girl. More loyal than any other girl I had met at that place.

I know you hate me and I am sorry. I know I did everything to earn your hate and what makes me angry with myself is that, that is the opposite of what I was going for. It was too late for me to realize you would have been a good friend. I am sorry for antagonizing you, refusing you to call you by your name, and for ruining our scene of Romeo and Juliet. I have excellent timing for ruining things.

I would not have written this stupid letter if my therapist hadn't made me, but the sentiment is true. You have my permission to hate me. I deserved it. I just have to ask, please don't tell anybody I have a therapist. I know about sixty percent of our classmates have one, but it would a punch in the gut if the God of Chilton had to go to one. Good luck with school.

Here's looking at you kid,

Tristan Dugrey.

* * *

Tristan finished the letter begrudgingly. He didn't do feelings. He didn't want to talk about them and sure, as shit didn't want to write about them. This was one more way to be embarrassed in front of the girl. But lets face it, after the past year and a half, there didn't seem to be any other way of acting around her. He gave a quick prayer that her character was as he thought, that she would keep his confidence. Hartford had a long memory and a Dugrey's humiliation would cast a long shadow. Long after he returned from Military school. He signed the letter and handed it to his therapist. It was out of his hands now.


	2. Chapter 2: Unexpected Response

**Dissclaimer: ** characters are owned by Amy Sherman Palladion

quote from 'thlema and louise'

* * *

Dear Tristan, Tuesday the 8th

I was shocked to get your letter. I needed to make a few things clear.

1. I would never spill your secrets to anybody. You were right it's not me. Plus I would never give those horrible people you call friends the satisfaction of have something over on you. Not that you have terrible taste in friends, it's just that, that place makes good people act in terrible way.

2. I don't hate you. Now, you were never my favorite person at Chilton. Can you blame though, you called me Mary even though you knew my name. Did you know that Mrs. Huber, our French teacher still calls me Mary because she honestly thinks that is my name? I found you irritating, but I never hated you.

I know you overheard me talking with my boyfriend that night of the play. Dean gets so jealous and I just wanted to stop fighting with him. I said that I hated you because it was the easiest way to get him to calm down. Ever since the dance you are a sore spot for him. I don't understand why boys need to become cave men when they perceive a threat. He didn't understand that you just liked to torment me.

I hate that you did something so stupid like break into the safe. '_You're a real outlaw aren't ya?' _You are so much more than that. Those last few days you were at Chilton I could see it too. We could have been friends there.

I hope you are adjusting to military school. It can't be easy. I know what its like being out of your comfort zone. I can imagine you king of the hill by now Ralph. Just please don't nickname somebody piggy, Mary was bad enough.

Your therapist told me it would be okay to write you back. He sent his own message. He said that cadets are not allowed unsupervised Internet access, but your letters are considered private. So I felt like it was safe to write you back.

Take care of yourself Tristan. We never made it to the friend's stage with secret handshakes and inside jokes but I wouldn't turn down any letters you sent. I'm not saying you want to write me, just that if you wanted to write me I would write you back. Not that you would want letters from me. Okay I am officially rambling. If this is goodbye Tristan… Good Luck

Rory Gilmore

* * *

Tristan read the letter twice before folding it neatly in eights and stuffing into the front breast pocket. He never in million years would have expected her to write back. Hell, she invited him to write her back. He closed his eyes and could picture the last time he saw her.

She was standing in the hallway with that giant ape telling how much she loathed Tristan. It was worse than anything his father had ever yelled at him. The girl he had a crush on hated him. He knew he had lost all hope of ever being with her. She preferred the freakishly tallboy next-door type. He could never be that guy, not even for her.

The question now was could he be man enough to write her back. Write her without having it be mandatory, with his therapist reviewing everything he wrote. She could have just said she would write back as a courtesy, not expecting him to actually write.

Tristan didn't have to think to hard about it. Besides the weekly call from his father and the care packages from his grandparents, he had no contact with any of his old friends. Out of sight out mind for them. They didn't need him to bank roll their misadventures. They didn't have a need for him.

"_I don't hate you"_ it wasn't an 'I like you', but it was a start. Tristan got up off his cot and finished making his bed for inspection. He would allow himself the rest of the day to decide to write.


	3. Chapter 3: Dear Rory

Rory, Monday 14th

I know I was never your favorite person at Chilton. Don't be so quick to judge everybody there as terrible people. I got caught because of poor timing and bad luck. My friends would never narc on me. Contrary to your opinion of the Hartford society, not all wealthy upper class males are self centered. We can make distinctions between friends, family and business. My mother is fond of saying "what happens in the board room will not be brought into the dining room". I am sure every lifestyle has a similar phrase.

My father told me how my great grandfather acquired the pharmaceutical company that has been the family's flagship business for the past 47 years. Grandfather was friends with Josiah Lilly before the war. One night over drinks they started to brag which was the better business man. Josiah was raving about how he was hiring this scientist who was on the brink of blowing all the competition out of the water. What Josiah didn't know was that my dear old Great Granddad wasn't as drunk as he claimed to be and he sent a message to his brother. That weekend while Josiah and Tristan Dugrey the 1st where enjoying the speakeasies of Chicago underground, Julian Dugrey took the express train to Indianapolis and offered the scientists double plus 1% of all royalties. Within a month Dugrey Inc. had a press release to announce the new drug, insulin. When Josiah passed away his obituary stated he counted Tristan as his greatest friend. He realized he had no one to blame but his own carelessness and loose lips. You have to compartmentalize or live with the consequences of being at an empty dinner table.

So that you don't think all Dugrey's are apart of an evil empire, they pharmaceutical company hired Josiah to stream line our manufacturing facility in the 20's and with their help made the penicillin that was sent with the GI's during the war.

Back to my point. I don't blame the guys for leaving me to take the fall. They didn't drag me to the safe I wanted to be there. Although it would be nice if there was a least one familiar face here, or a friendly face.

I know the strings my dad had to pull to get me here. I wonder if he googled, desolate, soul sucking academia to find this place. The classes are not up to par with Chilton. Every minute of the day is mapped out to remove all time to think freely. Community showers are only good when its the title of a movie with hot chicks on the cover. I am not being crass, just making a statement that they should be banned from real life experiences. I have a roommate, his name is Phil, and he hums while shaving. That is the extent of the information I know about him and I have shared a 10x7 living space with him for 2 months. He doesn't talk much. I find myself talking at him just to see what will get a reaction. Perhaps that is why I have rambled here. There is nobody to worthwhile to talk to who will engage in conversation.

I suggest you live a little Mary. The thrill of doing something because you can and you are young. You can't live forever in one of those books you are always toting around. Just don't do something that will land you here, unless you want to be my roommate, we can bunk, you can be on top.

I look forward to hearing from you.

Tristan

* * *

**So this was hard to write. Getting in his mindset. I think that Tristan has a lot of growing up to do. We only ever saw him when he was showing off. And because this is a letter it is only what he is willing to reveal to Rory. He hides behind his family name and flirtation. Let me know what you think. **

**Also. The story about the insulin…Josiah is a really guy, along with some chemists developed Insulin. But I took the liberty of stealing it. The Dugrey's have a lot of fingers in a lot of pots. **


	4. Chapter 4: The basket

**Disclaimer: ** I do not own characters from Gilmore Girls

**Notes: ** Feedback would be great. Also suggestions. Have an endgame planned but will always welcome suggestions

* * *

Friday February 18

Tristan,

I am sorry for judging you and your friends. I shouldn't have presumed to know what your relationships are like. I have one best friend. Her name is Lane and I try not imagine what the people of Stars Hollow think of our friendship. I honestly can't remember a time when she wasn't my best friend. If I was going to do something illegal it would be with her. We are really good at bending the rules already.

Lane's mom has a similar philosophy about business. She runs a antique store and she believes, "You want it, we got it, you like it you buy it, you break it...price doubles". When we study at her house you can never leave your books unattended. My mom had to track down a tourist and buy back my carved wooden pencil case Luke had made me for my birthday when Mrs. Kim sold it when I went to the bathroom.

You talk at your roommate. Do you ever ask him questions? I remember ignoring you too when you talked at me by my locker. I bet Phil's letters home are about his crazy roommate with the great hair who doesn't shut up. Is your school filled with other upper crust delinquents?

Chin up Wilbur. The semester is almost half way over and you will be home soon. You can survive a few more months. Your father will probably enroll you in nice co ed boarding school where you can find that bunk buddy you are searching for.

I am going to ignore your comments about the communal showers. However, while at Doosies market I found the enclosed item. I hope it helps.

I am currently taking a break from packing a picnic basket for the annual charity picnic basket. Every year the women fill a basket and the men bid on them for the contents and a date with the basket maker. The fun is not knowing who made the basket. Sookie always brings in a lot of money. She is the chef at the Inn. Two years ago she made a breakfast basket filled with waffles, pancakes and griddle to make omelets to order with seven different kind of cheese and the basket was made out of cinnamon bread. So far i have two stale pop-tarts and a slim jim.

I never knew I had this question, but I am dying to know. What do you do for fun at Military School? My current knowledge is from limited research. When I told mom that bible boy was going to military school she chose 'Taps' for movie night. I am honestly looking forward to your next letter Cadet.

Till Next time,

Rory


	5. Chapter 5: Free Time -T

**Disclaimer: ** I do not own the characters

**EDIT: ** Somebody kindly informed me of a few errors. Thankfully I never went to Military school so I didn't know.

**A/N: Thanks for the support. I am flattered that I have anybody following this story. Please let me know how you are liking the story if you have any suggestions. I didn't realize how hard an epistolary story would be. Untrustworthy narrators and all. Would you enjoy switching to some live action too?**

* * *

Thursday February 24

Rory,

Thanks for the soap on a rope, obviously you have a dirtier mind than you would like to people to know. The next time I am in the shower cleaning that great hair you seem to be fond of I will be thinking of you.

I will take you advice about Phil into consideration. I think I need some training in interrogation strategy to get past his silent treatment. What I have discovered so far, he gets care packages every other Tuesday from somebody, I'm guessing a woman based on all the baked goods. I get grunts in response to all my questions. The Dugrey charm is better suited to the fairer sex.

To answer your question about free time I will have to explain my day. Wake up at 5:45 am where I take that shower I told you about.

0620 inspection. Beds made and in uniform.

0630 breakfast in the mess hall. Did you know that scrambled eggs can come in liquid form in a plastic bag? I use the term eggs loosely. Some of the guys here are on scholarship and they work in the mess hall as part of the arrangement.

0700 Reveille

0730 our first block class begins.

0930 second block class begins

1130 drills

1230 lunch

1310 first block lab

1430 Second block lab

1535 manuevers

1630 Rec/drill/Study hall.

I actually joined the swim team here. They have an Olympic size swimming pool and it is my favorite part of the day where I can be submerged in the water. Everything fades away and its just me in the water. I don't need to be racing against somebody, just competing with myself to go faster. When my mind slips and I start to dwell on things I would rather set aside I count the hours till I can jump in the water.

I like being a part of the team too. The guys who do long distance are turning out to be good friends. JJ or Rat as the team calls him. Has been in some form of military school his whole life. His dad is Major in the army and its his family tradition to graduate west point. At least my family legacy doesn't require putting my life on the line, yet again there is less honor in making business deals on the golf course and pressuring your family to conform. I don't want to sound like I am complaining. I love my dad I really do. But I just know that he will always compare me to my brother.

Getting back on topic. Dinner is served at 1800 and we have free time till mandatory lights out at 2200 after TAPS

Weekends we have physical education and ROTC in the morning. If we still have priveliges we have leave to go into town. There is a small theater that in the afternoon shows old movies. Last week it was Arsenic and Old Lace. "Insanity runs through my family, it practically gallops" I highly recommend it for your next Gilmore Girl movie night. I invited Phil to join me and the swim guys next week.

Here's lookin at you kid,

Tristan


	6. Chapter 6: Family

**Disclaimer:** I do not own Gilmore Girls

**A/N:** Thanks for the support. I hope to crank out a chapter a week. Let me know if there is a particular episode you want me to address.

* * *

Dear Tristan,

I am offended that you would suggest I haven't seen every Cary Grant movie ever created. My mother has always prided herself on providing a well-rounded education. Our tastes range from PJ Harvey to the Runaways. I think the only movie genre we can't find the mildest form of appreciation is horror. I honestly don't know how people can find it entertaining to watch people be pursued, terrorized, brutalized and murdered.

Your day seems very organized. I thought it was bad having to wake up an hour earlier to reach the bus to take me to Hartford. Thankfully my commute allows me a small amount of time to read before I entering the lion's den. I love to read. Being swept away on an adventures, love, heartache and worlds more colorful than ours. When I reach the schools gate I have to put those daydreams away and be alert. Do society women teach their young how sharpen their claws on those they presume to be weaker?

I feel like I am losing control all the time. The basket auction did not end they way I had hoped. Dean lost the bid to Luke's nephew Jess. Jess is new in town and he has not made any friends in town. Luke is surely on his good days and that can't help, but we all love Luke. Jess just seems to try and piss people off. I think he was the one who stole Pierpont. But he is nice to me. I understand what it feels like to be the new guy in an established community so I want to be nice too. But it just makes Dean angrier. He has turned me on to Charles Bukowski. I will let you know how it goes.

My Dad is making an appearance in my life again. I have learned not to get my hopes up where he is concerned. I fail miserably. This is the first time he introduced me to a girlfriend. Mom was not happy, I could tell, when I agreed to spend time with her. I know my parent fought when I was there.

I am envious that you have a sibling. I don't think my parents will ever have another kid. I mean my mom was close when she agreed to marry max, but that just didn't happen. I know she said it was her decision to end things that she was just looking out what was best for her and us. It just makes me so angry how she ended things. I never thought my mom would ever do something so mean. It would be nice to be able to share with a kid sister or brother. It wouldn't feel so suffocating to be the center of attention. I would prefer to have a back seat, like journalists in the wild, observing without obligation of participating.

I am glad you are making attempts with Phil and this Rat kid. I hope his nickname doesn't' stem from his character. Would you believe that I think Paris and I are less 'mortal enemies' and more 'cool acquaintances'? I think its blossoming into a lovely friendship, ha.

Sending you something to help with the friend department. Sookie is in a baking frenzy testing new recipes for the Inn and her wedding. My stomach is legendary but even I have to draw the line somewhere.

Till next time bible boy,

Your friend?

Rory

* * *

**Dear Rory,**

"Your friend?" Yes I think these last few letters have put us on the path the friendship, but don't think for a minute this means the kind of sleepovers where we braid hair and read 17 and discuss the cuteness of Justin Timberlake's butt.

Give Sookie a kiss for me. Those cookies were equivalent of culinary orgasms. Sadly they did not help with making friends because I ate them all. Can I have her contact information; I need to be kept stocked in her wares.

I am not going to touch the subject of this Jess character. You won't like what I have to say. I am sorry that you feel so alone a Chilton. FYI, everybody feels that way. Don't perceive yourself as the sacrificial lamb being brought to the slaughter, you are so much more than that.

I do have siblings, two little sisters, Rose and Violet. They are ten years old so you have the misfortune of never being in school with them. They are terrors. They are identical and have a ravenous appetite for mischief. I love them dearly. For ten year olds they have much clearer understanding of what is and isn't appropriate. My father has sent them to boarding school too. However, there school comes with horses so I am fairly sure they are content. Dad does love the concept of children should be neither seen nor heard.

I had an older brother.

I think that Rory Gilmore should never sit in the corner. You should be out there in thick of it. Its what the great novelists and journalists did. Isn't there an adage of write what you know? So live a little Gilmore.

Here's looking at you kid,

Tristan


	7. Chapter 7: Live a little

OKAY I have a question. Would you mind if I switched from epistolary to more live action narrative? I have an idea for the next few letters. But after that it could go either way. Also. Thought on whether or not stick to canon of the Logan storyline? Again I can make it go either way. But fan fiction is for the fans and I always appreciate input. THANKS AGAIN FOR ALL THE LOVELY SUPPORT. I hope this chapter wasn't too rushed.

These letters are over the course of about a month.

* * *

Mary,

I don't even want to know how you got Justin Timberlake's face on cookies. Do you have any idea the shit I got when I opened those? Haha. Real smooth thanks. Phil actually showed a human emotion and laughed. He's not such a hard ass.

Here's looking at you kid,

Tristan

(Enclosed a picture of four cadets eating cookies that look like Justin Timberlake)

* * *

Tristan,

Are we back to calling me Mary? I remember very clearly during the Shakespeare exam stressing that my name is Rory. I only sent those cookies to help you get a slumber party started, because clearly you have given a lot of thought to what goes on at them. Plus you were able to positively identify Justin from a cookie likeness. Hope you have a good weekend. I am looking forward to a quite weekend here. Grandma tricked my mom into a spa weekend. I am going to go wild and do laundry, watch some TV and order Indian Food.

I can give you Sookie's contact information for formal functions. She does cater. But I can send you the stuff not on the menu. This week she decided to invent a new salty candy dessert. She couldn't figure out what it was missing. Than she realized she was craving caramel. I helped roll those bad boys in wax paper for some pocket money. There are over 400 pieces. Share.

Are you ever coming back to Hartford?

Rory

* * *

Mary,

I will continue to call you Mary when you act like her. I happened to like her. I see you still need to work on you idea of living a little. When my parents where out of the house there was always a party. I remember when I was 11, my parents left for two weeks on business in Berlin. Everyday the house was filled with friends. My brother Eddie had set a casting call for models and hired them to be the staff for the week. The girls where staying with Grams so we didn't have to worry about them tattling. I was in awe; the house was filled 24/7 with beautiful people. Girls and guys fully clothed where swimming in the fountain. Strangers were camping on the Tennis Courts. It was two weeks of eating cereal and anything that we could pop in the microwave until my brother hired caterers. He said nothing was too grand for the Hartford crowd and pizza delivery was not going to cut it. I have no recollection of how Eddie was able to convince our grandparents to let us stay home. He had a way with words and charming the pants off of anybody. When you were with him, you felt like you were the center of the universe. "Stick around Trey, the world is ours for the taking."

I am hard pressed to admit that TV and Indian food doesn't sound too terrible. It would just be nice to have some company. You should check out the show 24. It's a favorite here. I think you should try one thing new this weekend. You don't have to travel to expand your horizons.

I hope to come home for a weekend next month. It's my grandmother's birthday and she always throws a great party. Last year she wanted a roman themed party. You haven't lived Mary, unless you have seen the mayor of New York trying to wear a toga and negotiate a deal for NYC to be the headquarters for a new division of Dugrey industries. Are you asking me out miss Gilmore?

Phil says thanks. He likes the caramel. I had to explain to him who you were. First off, he thought Rory was a boy and I had to subsequently explain how I wasn't a homosexual. Don't ask, don't tell, my ass. Apparently he had seen some addressed letters and he thought I was pining for some boy back home. That I had been caught in the act and that was why I was sent here. I couldn't stop laughing. O, if he only knew Mary. O, if he only knew.

Here's looking at you kid

Tristan

* * *

Tristan,

Sometimes I wish I was already a grown up, Or at least considered to be one long enough to avoid having to be accountable of all my actions to somebody else.

I would have gladly traded my weekend for one of the burgouise you brother seemed to favor. It was terrible. First off, Paris showed up to study. Than Jess came by with food and he wouldn't leave. I don't understand him. He says he wants tot be friends but than he does the exact opposite of what I want him to do. He thrills in causing trouble. If Paris hadn't been there I don't know what Dean would have done. Dean showed up with Ice Cream just as I was successfully able to force Jess out.

I have to hand it to Geller; she is quick on her feet. She kind of sort of convinced Dean that she had arranged for Jess to be there for them to hook up. I honestly don't know what to do in this situation. I mean, why am I getting punished because of the actions of somebody else? Doesn't he trust me? I thought when you loved somebody you trusted them.

It has now become overbearing. He just won't let me have breathing room. This past week we have been working on our entrepaneur project. My Grandpa was our advisor and we came up with a clever product line. It was actually fun working on it. Richard is the only one who ever seems to treat me like an adult. However, I will never be able to confide in him the coming and goings of a teenage girl. I think his teenage daughter getting pregnant at sixteen was too much for him. He prefers our conversations to be curtailed to business, books and scholarly pursuits.

Right now mom and I are working on picking out a movie for movie night in Town Square. I think the yearling is going to win out. I was rooting for Casablanca but something about royalties. Perhaps it's your sign off that keeps that movie on the forefront of my mind.

Can I just say? Without you reading too much into it. I would be lost without these letters. It's better than a journal, you write back. You never seem to judge me, besides my lack of ever having done anything. It is just nice having somebody who doesn't already have formed opinions about the people in my life. I don't have to worry about offending you. I hope we can meet up when you come to Hartford. I know you have your Chilton friends you want to see, but maybe a cup of coffee?

Now I have officially rambled too much.

Your Friend

Rory


End file.
